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      Symbioimine and neosymbioimine, amphoteric iminium metabolites from the symbiotic marine dinoflagellate Symbiodinium sp.

      Bioorganic & Medicinal Chemistry
      Animals, Cell Line, Dinoflagellida, chemistry, Heterocyclic Compounds, 3-Ring, isolation & purification, pharmacology, Magnetic Resonance Spectroscopy, Mice, Molecular Structure, Spectrometry, Mass, Electrospray Ionization

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          Abstract

          Two amphoteric iminium metabolites, symbioimine (1) and neosymbioimine (2), were isolated from a cultivated symbiotic marine dinoflagellate Symbiodinium sp. Compounds 1 and 2 have a characteristic 6,6,6-tricyclic iminium ring structure and an aryl sulfate moiety. The plausible biogenetic pathway of 1 and 2 can be explained by an intramolecular Diels-Alder reaction followed by imine cyclization. Symbioimine (1) inhibited the differentiation of RAW264 cells into osteoclasts (EC50 = 44 microM), and significantly inhibited cyclooxygenase-2 activity at 10 microM. Thus, symbioimine is a potent anti-resorptive and anti-inflammatory drug.

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